

Retire With Purpose - The Retirement Podcast
Casey Weade
Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and Founder of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2024 HOWARD BAILEY FINANCIAL, INC.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and Founder of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you've always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2024 HOWARD BAILEY FINANCIAL, INC.
Episodes
Mentioned books

Jan 30, 2026 • 31min
546: Freedom After 50: How to Stay Grounded When the Future Feels Unknown
What if the key to a calmer, more meaningful retirement isn't having all the answers, but learning how to trust yourself when you don't? In this episode, we discuss: Why retirement feels more uncertain than working life How identity shifts after 50 can create anxiety What's true vs. what's just loud How to focus on what you can control — in life and money A 4-step practice to calm fear and regain clarity Today's article is from our very own blog titled, Approaching Uncertainty with Yada. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade is joined by Les McDaniel to explore why retirement can feel more uncertain than working life. Show Notes: HowardBailey.com/546 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu 📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

12 snips
Jan 23, 2026 • 33min
545: By the Numbers: Our 2026 Market Predictions
Will 2026 bring a bull market or a reality check? Predictions range from 6.7% to a bullish 15.2% for the S&P 500. The role of AI in the market is pivotal, yet adoption rates lag behind expectations. The Magnificent Seven's influence is declining, prompting a shift to equal-weighted investing for stability. Global diversification and the revival of bonds are essential strategies. Pre-retirees are advised to protect their gains while considering market volatility and potential corrections.

9 snips
Jan 16, 2026 • 26min
544: Freedom After 50: Are You Living for Your Resume—or Your Eulogy?
Join certified retirement coach Les McDaniel as he dives into redefining success after 50. Discover the compelling contrast between resume virtues and eulogy virtues, exploring why many retirees feel lost despite their achievements. Les encourages a shift from mere accomplishments to a focus on who you want to be remembered as. Learn how financial planning can align with your purpose, and hear personal stories of transformation that illuminate the path to a meaningful retirement.

15 snips
Jan 12, 2026 • 1h 1min
543: The Stress Paradox: Why the Right Kind of Stress Helps You Thrive in Retirement with Dr. Sharon Bergquist, MD
Join Dr. Sharon Bergquist, a board-certified physician and founder of Emory Lifestyle Medicine & Wellness, as she explores the surprising benefits of stress in our lives. Dr. Bergquist shares how early adversity influenced her research into resilience and why not all stress is detrimental. She emphasizes the importance of 'good' stress in retirement for maintaining health and growth. Discover how purposeful challenges, recovery practices, and a mindful approach can enhance well-being and longevity. Plus, learn about the powerful connection between purpose, resilience, and biological aging.

20 snips
Jan 9, 2026 • 36min
542: By the Numbers: From Fear to Freedom — Learning How to Spend in Retirement
Struggling to spend in retirement? The hosts tackle why many retirees underspend despite solid financial plans. They explore the emotional barriers that arise from lifelong saving habits and how these habits impact spending choices. Strategies to boost spending confidence are discussed, including practical 'spending experiments' to test new financial behaviors. The conversation emphasizes the importance of aligning personal identity with spending to encourage a more joyful retirement experience. Tune in for insights on navigating this complex emotional landscape!

8 snips
Jan 2, 2026 • 38min
541: Your 2026 Reset: The Best of the Retire With Purpose Podcast
Discover the top retirement regrets that many face, with a staggering 76% wishing they had saved more. Explore innovative income strategies that surpass the traditional 4% rule, focusing on dynamic, market-aware methods. Learn about the Surplus Bucket Strategy, designed to boost spending confidence through liquid savings. Additionally, understand the importance of both financial and nonfinancial preparedness as you assess your retirement readiness. Casey Weade emphasizes the joy of balancing memories and money for a fulfilling retirement.

7 snips
Dec 26, 2025 • 21min
540: Freedom After 50: The Quiet Fear Beneath Retirement (and How to Outsmart It)
Les McDaniel, a retirement coach and author, shares insights on the pervasive sense of unease many face upon retiring. He explores how external factors like news can heighten anxiety, even in those with solid financial plans. Emphasizing the importance of presence and self-awareness, Les introduces the Yada reflective framework, encouraging listeners to cultivate inner peace through techniques like journaling and self-reflection. He also highlights the futility of seeking external validation and true wisdom in others.

12 snips
Dec 19, 2025 • 31min
539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions
Discover the surprising benefits of capital gains harvesting and why some retirees choose to realize gains instead of losses. Learn about the 0% capital gains bracket and the strategic timing for tax planning around Social Security and RMDs. The discussion dives into whether tax gain harvesting or Roth conversions offer better long-term savings, with insights on the implications of converting IRAs. Tune in for a fresh perspective on navigating taxes to maximize your retirement portfolio.

7 snips
Dec 12, 2025 • 26min
538: Freedom After 50: Why Enough Is a Mindset, Not a Number
Les McDaniel, a certified retirement coach and financial advisor, joins the discussion on redefining what 'enough' means in retirement. They explore how believing one never has enough can hinder joy, revealing the perils of oversaving and the downsides of the FIRE movement. The conversation shifts to the importance of pursuing curiosity and creativity over constant striving, emphasizing that self-worth should precede financial wealth. Ultimately, they advocate for using money to enable meaningful experiences rather than simply chasing a number.

24 snips
Dec 8, 2025 • 1h 7min
537: The Most Overlooked Elements of a Successful Retirement with Fritz Gilbert
Fritz Gilbert, an award-winning blogger and author of The Retirement Manifesto, shares insights from his six-year retirement journey. He discusses the emotional evolution of retirement, emphasizing the importance of giving yourself permission to spend and enjoy life now rather than later. Fritz reveals how to intentionally reshuffle priorities, avoid the common retirement pitfalls of boredom and identity loss, and maintain fulfillment through continued learning. Plus, he offers unique strategies for financial planning to enhance satisfaction.


